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DOS 2 220 246 (ICN; Anm. 25.4.1972; USA-Prior. 1.6.1971. 31.3.1972). DOS 2441823 (ICN; Anm. 12.3.1974; USA-Prior. 12.3.1973).
DOS 2511 828 (ICN; Anm. 18.3.1975; USA-Prior. 18.3.1974).
J-Anm. 75 123 883 (Kyowa; Anm. 15.3.1974).
USP 3 976 545 (ICN; ert. 24.8.1976; Prior. 1.6.1971).
USP 4138 547 (ICN; ert. 6.2.1979; Prior. 22.12.1977).
Struktur und Konformation:
G. P. Kreishman et al., J. Am. Chem. Soc. 94,5894 (1972).
USA: Vilona® (ICN) Virazole® (ICN)
Viramid® (ICN)
Riboflavin 83-88-5 Vitamin
(Lactoflavin,
Vitamin
7,8-dimethyl-10-(D-ribit-l-yl)isoalloxazine
806 R Riboflavin
1 A/-(314-Dimethylphenyl)-D-nbamir s Q]
H3C.
НзС'
xr
2 Riboflavin
ш
CsHs — N? Cl SenzoWiazfl-rmmchiofid
CH20H
ho-c-h
I
ho-c-h
I
HO-C-H
I
o' н
CH2OH
(НО-С-Н)з
CH
II
H3Cn^Yn
H3C^^
3,4-Dimethylamlin D-Ribose
CH2OH
(НО-С-Н)з
НзС,
НзС
XT
CH2
NH
ш
но он я- сн2он
О- Ribonsaure-lacton
н3с
CH20H
(НО-С-Н)з
с=о
I
Н3С‘
:хг"
Нг/Си-Сг^Оз oder Hi/Ft
ш
СН2ОН (НО —с —Н)з сн2
НзС.
н3с
МИ
XX
;>v^4M=N-C6H5
,NyO
-NH
Riboflavin
Na2S20t
Natrumdi-
thionit
CH2OH
(НО-С-Н)з
CH2
, ^ NH
a USP 2 384 105 (Roche; ert. 1945; Anm. 1943). b USP 2 411611 (Roche; ert. 1946; GB-Prior. 1941).
USP 2422 997 (Roche; ert. 1947; Anm. 1944).
DAS 2 558 515 (BASF; Anm. 24.12.1975) - Hydrierung an Cu-Cr203. DAS 2558516 (BASF; Anm. 24.12.1975)- Hydrierung an Cu-Cr203. Altemativ-Verfahren (aus 3,4-Dimethylnitrobenzol):
DOS 2 650830 (BASF; Anm. 6.11.1976). с M. Tishler et al., J. Am. Chem. Soc. 69,1487 (1947).
USP 2 350 376 (Merck & Co.; ert. 1944; Anm. 1941).
USP 2 370093 (Merck & Co.; ert. 1945;Anm. 1941).
Ahnliche Verfahren:
M. Tishler et al., J. Am. Chem. Soc. 67,2165 (1945).
USP 2 807 611 (Merck & Co.; ert. 1957; Anm. 1955). d P. Karrer и. H. Meerwein, Helv. Chim. Acta 18,1130 (1935).
R. Kuhn u. F. Weygand, Ber. dt. chem. Ges. 68, 1282 (1935).
Riboflavin - Ribostamycin R 807
Fermentative Verfahren:
USP 2445 128 (USA-Secret. Agriculture;ert. 1948; Anm. 1946),
USP 2 483 855 (Commercial Solvents Corp.; ert. 1949; Anm. 1942).
USP 2 876 169 (Grain Process. Corp.; ert. 1959; Anm. 1956).
USP4 165 250 (Merck* Co.; ert. 21.8.1979; Prior. 29.8.1975, 22.3.1976, 14.11.1977). Isolierung aus Fermentationsbriihen und Reinigung:
USP2387 023 (Commercial Solvents Corp.;ert. 1945;Anm. 1944).
USP2421 142 (CommercialSolventsCorp.;ert. 1947; Anm. 1944).
USP 2 367 646 (Commercial Solvents Corp.; ert. 1945; Anm. 1943).
USP 2 571 896 (Merck & Co.; ert. 1951; Anm. 1945).
USP 2 797 215 (Commercial Solvents Corp.; ert. 1957; Prior. 1951,1955).
USP 4165 250 (Merck & Co.; ert. 21.8.1979; Prior. 29.8.1975, 22.3.1976, 14.11.1977).
D; Beflavin® (Roche) I: Beflavina® (Roche)
zahlreiche Komb.-Praparate Vitamin В 2 Asolo (Vis)
F: Beflavine® (Roche) Vitamin В 2 Vis (Vis) Riboflavine B.O.N. (Adrian-Marinier)
RibOStamycin 25546-65-0 Antibioticum
(Ribostamin) 53797-35-6 Sulfat
0-2,6-diamino-2,6-dideoxy-a-D-gIucopyranosyl-(l—»4)-0-[/S--D-ribofuranosyl-(l—»5)]-2-deoxy-streptamine
a Durch Fermentation aus Streptomyces ribosidicus ATCC 21294.
b
0 0
R-O-CO-NH
OH
R = Ch2-C6H5 k
4-0-(2,6-Bis- [еп2у1охусагопу!ат)ПО-3/-^-0-benzyl-2,6-dideoxy-a- 2Д5-Tri-0-benzoyl-O-nbosylchlond D-glucopyranosyl)- Nt N'-bis-(benzylaxycarbonyl)-2-deoxystreptamin
R —0—CO—NH —CH?
NH —CO —0 —^
0 0
r=ch2-c6h5
R R
1. NaOCHj
2. Pd-C/H2
HO OH
Ribostamycin
808 R Ribostamycin - Rifampicin
a DBP 1 814 735 (Meiji Seika Kaisha; Anm. 14.12.1968; J-Prior. 15.10.1968,18.12.1967).
T. Shomura et al., J. Antibiot. 23,155 (1970). b DOS 2 104129 (Meiji Seika Kaisha; Anm. 29.1.1971; J-Prior. 2.2.1970).
Weitere Verfahren:
DOS 2 537688 (Hoechst; Anm. 23.8.1975).
JP 54008792 (Shionogi; Anm. 16.6.1977).
JP 53 201 155 (Suami; Anm. 10.8.1976).
T. Suami et al., Carbohydr. Res. 56,415 (1977) und dort zitierte Literatur.
Totalsynthese:
H. Fukami et al., Agric. Biol. Chem. 41,1689 (1977).
D: Landamytine® (Delalande) 1: Ibistacin® (Ibi)
F: Ribomycin® (Delalande) J: Vistamycin (Meiji)
Rifampicin 13292-46-1 Antibioticum
(T uberculosemittel)
3-[[(4-methyl- l-piperazinyl)imino]methyl]rifamycin SV
C22H36O5
0-СН2-ССЮН
Rifamycin S
(aus Streptomyces medi-terranei ATCC 13685)
С22Н35О5-CO
HO 0
NH
Rifamycin 0
C22H ЗбОб'
Rifamycin S
C22H36O5
Rifamycin SV
ch2o/hn
a
С22НЭ605'
3-Pyrrolidinomethylrifamycin SV
I РЫ0-С0-СН3)4 /СН3СООН iСНС13 2. wassr AscorbiDsaure 1. Blei(IV]-acetat
C22H36O5-CO
но он
NH CHO
снз"-
3-Formylrifamycm SV
l-Amino-4-methyl-pi perazin
Rifampicin - Rimiterol R 809
N. Maggi et al., Chemotherapia 11,285 (1966).
USP 3 342 810 (Lepetit; ert. 19.9.1967; GB-Prior. 31.7.1964). DAS 1795 567 (Lepetit; Anm. 28.7.1965; GB-Prior. 31.7.1964). Alternati v-Verf ahren:
DOS 2 846 321 (Holco; Anm. 24.10.1978; GB-Prior. 25.11.1977). Fermentative Gewinnung von Rifamycin B:
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